


Little Help from My Friends

by casual_distance



Series: More Than One [1]
Category: Supernatural
Genre: Alternate Universe, Alternate Universe - College/University, Bet Making, Circle Jerk, Coming Untouched, Dirty Talk, Fantasizing, Flirting, Friends With Benefits, Friendship, Kissing, M/M, Masturbation, Multi, Porn Watching, Sex Toys
Language: English
Status: Completed
Published: 2016-04-24
Updated: 2016-04-23
Packaged: 2018-06-04 03:20:41
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 4,030
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6639313
Author URL: https://archiveofourown.org/users/casual_distance/pseuds/casual_distance
Summary: <blockquote class="userstuff">
              <p>“I get by with a little help from my friends.”  Alternately: I get off with a little help from my friends- a fic in which Dean has <i>very</i> good friends.</p>
            </blockquote>





	1. Little Help from My Friends

**Author's Note:**

> So, trying to decide how to tag the relationships in this was hard. I ended up tagging only Dean/Cas and Cas/Gabe because they’re the only relationships that have romantic implications in this fic, Dean/Cas presently and Cas/Gabe (mostly) in the past. 
> 
> Otherwise, you can expect: Cas/Gabe flirting, Balthazar/Aaron flirting, Balthazar/Aaron/Samandriel flirting, and Dean/Benny BFFs-4eva cuddling (plus a mention of past hook ups). Benny/Andrea is a background thing, and Benny is there with Andrea’s full knowledge and approval.
> 
> By “flirting” I mean there are sexualized interactions of various types. :)
> 
>  **Potential trigger warning for incest** : It’s mentioned that Cas and Gabe are technically step-brothers, but there’s no actual sibling relationship between them other than the label. (Cas and Gabe knew and were involved with each other before their parents met, though that’s not explicitly said in the fic.) There are some incest-as-a-kink jokes made during this discussion.

Dean settled down on the couch next to Benny, laughing at Aaron's story about the latest blind date his mother had set him up on.

"Then, when I asked him what he thought he was doing, he said that his mother told him to spend the night at my place. I was like, uh..."

"His mother told him to stay over?" Samandriel asked, incredulous.

Aaron snorted. "Come to find out the guy's not even gay. He didn't know we were on a date. His _mother_ had a date and wanted the house to herself."

Dean howled with laughter, rolling into Benny's side while Balthazar crowed and Samandriel gaped.

"I guess you let him spend the night," Benny chuckled.

"Yeah, poor guy crashed out on the couch. He could barely look me in the face the next morning, but I assured him no hard feelings. Date was shit anyway."

Dean rubbed the tears from his eyes as he pushed himself upright. Benny's arm curled around his shoulders and Dean relaxed back into him.

"Is Gabriel coming?" Balthazar asked. He thumbed his phone on and squinted at the screen. "I have an appointment after this."

"Yes," Samandriel answered. "He messaged me and said he was bringing someone-"

Samandriel cut off as the front door swung open. Gabriel sauntered in, another man trailing behind him. Gabriel gestured for the man to go sit while he closed the door and locked it behind them. Dean and the others perked up, watching the newcomer shed his overcoat and tug at his tie until it lay loose around his neck. He was good looking- near the same height as Dean with tanned skin and a shock of dark hair. The loss of his jacket showed off a lithe body, and the stretch of his clothes across his shoulders and arms gave away the hidden bulk of muscle. Dean absently palmed himself through his pants as he took in the new man, hoping he was willing to get naked today even if it was his first time with the group.

He and Gabriel muttered back and forth to each other as the man shrugged off a suit jacket, his face dark with irritation. Gabriel settled their debate with a dismissive scoff. He slung his arm over the man's shoulders, forcing him to slouch, and dragged him over to the group.

"Hey, guys!" Gabriel smirked and jerked the man onto the loveseat, plopping down close to him and settling a hand high on his thigh. "This is my brother, Cas."

Dean raised his eyebrows, casting a glance at the other guys. Aaron look scandalized while Samandriel looked ready to bolt. Cas sighed heavily and picked Gabriel's hand up by the wrist to drop it in Gabriel's lap.

"We're not really bothers," he told the group. Dean swallowed heavily, Cas's low voice tugging at the arousal that had already settled in Dean's gut. "Gabriel and I are technically step-brothers, but our parents only married this last year."

Gabriel shrugged and stretched an arm across the back of the loveseat. Aaron's expression eased, but Samandriel still looked uncomfortable.

"Didn't know incest was a kink of yours, Gabe," Dean teased.

Gabriel snorted. "You don't know a lot of my kinks," he leered. "Cas, that's Dean. His cuddle slut is Benny. You know Balth." Cas nodded. "Those two are Aaron and Samandriel."

"Hello," Cas greeted. "Gabriel said it would be alright if I joined you."

"Yeah, sure," Dean agreed easily.

"Do you know what you're joinin', brother?" Benny asked.

Aaron made a face. "Yeah, Gabe's not that good at explaining what this is exactly."

Cas rolled up his sleeves and pulled his shirt from his pants, letting it fall loose around his thighs. "I was under the impression that this is a masturbation group."

"It is, but the last time Gabe brought someone they thought it was a book club," Samandriel said with a dirty look at Gabriel.

Gabriel shrugged. "I was using a euphemism for polite company."

"He brought a book. A book you told him to bring," Aaron pointed out.

Gabriel grinned with a chuckle. "Yeah."

Cas elbowed Gabriel in the side. "Yes," he said to the group while Gabriel clutched his side and sent a wounded look at Cas. "I am aware. Although he did mention something about a challenge?"

Dean groaned and covered his face with his hands, slinking down into Benny's side. He chuckled and patted Dean on the shoulder.

"It's not a challenge per se," Aaron answered.

"We also loosely consider ourselves a hook up group, Cassie," Balthazar explained, "with the exception of Dean. So our challenge has evolved into us attempting to _not_ touch each other."

Cas raised an eyebrow and looked over at Gabriel, who shrugged. "The real idea is to get Dean to touch you." Dean protested, but Gabriel spoke over him, "But we sorta expanded it to everyone. There's a forfeit for whoever touches someone else."

"Ah," Cas acknowledged, his eyes tracing over Dean’s body, sending a flush to Dean's face. He met Dean’s gaze for a long moment, before he turned to drag Gabriel's arm off the couch and press it back into his lap. "That means you keep your hands to yourself then, Gabriel."

Gabriel leered. "You like when my hands wander."

Cas sniffed and faced forward, settling comfortably against the back of the loveseat.

Benny pulled his arm out from behind Dean and Dean shifted away. Aaron grabbed the controller for his Playstation and flicked on the TV.

"Cas, do you have a preference?" he asked. "Samandriel and I are gay, but the rest of the guys don't care who shows up in their porn."

Cas shook his head. "I don't have a preference either."

Aaron nodded and cast a glance at Samandriel who also shook his head.

"Anyone else?" Aaron offered to be met with negatives.

Aaron navigated to the hard drive he'd set up on his network and flipped through the videos saved there. He ended up picking a group scene with men and women, though it focused heavily on the men.

Dean slouched down on the couch, splaying his legs. Benny shifted, parting his knees, the one closest to Dean bumping against Dean's thigh. Samandriel sat in Aaron's beanbag chair, his legs folded up. His arm moved every so often belying the fact that he was already touching himself, but otherwise, nothing was visible of his arousal. Balthazar and Aaron stretched out on the floor side-by-side, heads propped up on throw pillows, feet brushing against each other. Both worked their pants open. Balthazar pushed his down to his thighs, while Aaron left his loose around his hips. On the loveseat, Gabriel had already pulled his pants off completely, leaving his t-shirt on, and had one leg draped over the armrest. His other leg was stretched out in front of him and he would kick at Cas's foot every so often, earning a dark look in return.

Dean watched as Gabe shifted downward, legs spreading wider. His cock was already hard and resting against his stomach, but he wasn't touching. Instead he reached down to play with the butt plug that he had in his ass already. He twisted it, pulling it out with a slow drag before pushing it in sharply.

Dean watched Gabe for a moment before his eyes wandered over to Cas. The man had imitated Dean and slouched down with his legs spread wide. He'd unbuttoned his shirt and it gaped open, giving Dean a glimpse of Cas's muscled chest. Cas's pants weren't undone yet, but they were tented. His hand rested on his thigh, but he shifted every so often to tease fingers down the inside of his thigh and then up over his balls and the line of his cock through the pants. Dean watched, entranced by his slender fingers and the graceful ease with which they moved.

Next to him Benny shifted and cleared his throat. Dean glanced up to find him watching Dean with a raised eyebrow. Dean frowned back and turned his attention to the TV where the camera was focused on a man bent over a table, a woman on her knees before him, sucking him off, while a man kneeled behind him, his fingers in the woman’s pussy, his tongue up the man's ass.

Dean groaned; he'd been both the man over the table and the man on his knees before, and the sight brought back pleasant memories. He unbuttoned his pants and eased down his zipper, sighing as his cock pushed out the opening of his jeans, thankful he'd forgone underwear. His cockhead shone damp with precome and Dean stroked his fingers across it before he pushed pants further down. He glanced around the room again.

Benny had also pulled out his cock, pants shoved up under his balls. He stroked himself with a steady rhythm, attention on the video instead of the other men in the room. Dean moved on, not ready to touch himself yet, and saw that Balthazar and Aaron had stripped down and were turned on their sides to face each other. He elbowed Benny and pointed with his chin; they were toeing the line. Benny grunted and sped up his stroke as he watched Aaron and Balthazar move with the same rhythm, muttering back and forth to each other too low to hear.

Dean looked away to find that Samandriel had shifted in the beanbag, stretching one leg out to give himself room. Both hands were in his sweatpants now. Dean could see the outline of one hand moving up and down over his cock, the head catching wetly on the fabric. Dean couldn't see what his other hand was doing, but from the movement of his shoulder, Dean guessed he had a few fingers in his ass. Samandriel was watching the video for the most part, but every so often he would shift and watch Balthazar where he had rolled over onto his back and was fucking up into his hand with slow deliberate rolls of his hips.

Dean watched Samandriel for a few moments, letting his head rest back against the couch. He finally gave in and fisted his cock, stroking up and down slowly, twisting occasionally over the head. His eyes traced over the line of Samandriel's cock through his pants. They were thin and with each brush of his cock against the material, the damp spot widened and the fabric stuck, teasing Dean with the shape of Samandriel’s cockhead.

Gabriel groaned, drawing Dean's attention to the loveseat. He rolled his head to the side to find that Gabriel now held a controller. Dean caught the faint buzz of the butt plug and smirked to himself. Gabriel still wasn't touching his cock. One hand clutched the controller and the other flexed in the fabric of the loveseat.

Next to Gabriel, Cas had finally opened his pants. His shirt was off, draped over the arm of the love seat. Dean bit back a moan at the sight of Cas’s chest; his pecs and abs were well defined, with a tattoo curling around his side. Dean watched the flex of his shoulders as Cas lifted his hips and pushed his pants down. For someone just now getting out of his pants, his cock was an angry red, and, as it bobbed, Dean could see the shine of precome smeared over the head and down the length. Cas settled back against the couch and reached down between his legs, where Dean realized he was playing with a toy as well. Gabriel flicked the controller and both men groaned, Gabriel rolling his hips, Cas arching his back.

Dean moaned, hand tightening over his cock as he realized that they were using synced plugs. At Dean's noise, Gabriel and Cas turned to look at him. Gabriel smirked and winked, but Cas held his gaze for a moment before his eyelashes dropped low. A slow, warm smile curled Cas's lips and he turned away after a second glance up at Dean.

Dean watched him for a little longer, fascinated with the sharp line of his jaw. Cas tipped his head back and swallowed heavily, eyes fluttering closed. His hips would jerk occasionally, body curling in on itself slightly with the stimulation of the plug as Gabriel played with the vibrations.

Dean lay back and closed his eyes. Aaron had left the volume low, and over it Dean could hear the wet, slick sounds of hands moving over cocks, the low groans and moans as they all got closer to coming. Balthazar muttered something that had Aaron giving a small, breathy laugh which dissolved into a moan. Samandriel made a small noise in his throat, one that had Dean opening his eyes to watch; he knew that sound meant Samandriel was close.

In the beanbag, Samandriel lay with his head tipped back, mouth open, small noises escaping him as the outline of his fist moved sharp and fast in his pants. In his periphery, Dean could see both Balthazar and Aaron twisted around to watch. Benny grunted next to him, his hand picking up pace.

Samandriel came first, his hand pressed to his mouth, his body curling forward over his lap as he stroked himself through his orgasm. Dean watched, hand moving roughly over his own cock, mouth dropped open at the spread of dampness in the front of Samandriel’s sweatpants. As Samandriel's body uncurled and he relaxed back into the beanbag, Aaron groaned from his place on the floor, coming over his stomach.

"Hah!" Balthazar barked and rolled to his knees.

"No!" Aaron wiggled away, but Balthazar swung his leg over both of Aaron's and pinned him in place as he stroked himself a few more times and came on Aaron’s chest, shaking his dick to spread the come around. Aaron groused and pushed at him, laughter under his complaints. Balthazar sat back on his heels and slapped at Aaron's thigh.

"That's what you get for coming first."

Aaron grumbled a complaint and went limp against the floor. Next to Dean, Benny made a choked noise. Dean glanced over in time to watch his mouth fall open, head tipped back, eyes squeezed shut, chest rising and falling heavily, his hand cupped over his the head of his cock as he came into it. He relaxed into the couch as he came down. Dean smirked at him when Benny finally cracked his eyes open; the few times they’d hooked up, Dean had had fun exploiting Benny’s domination kink. Benny rolled his eyes at Dean, knowing where his thoughts had gone, and elbowed him in the side.

"We've got three contenders left," Balthazar commented. "Shall we up the ante?"

He crawled over Aaron to Samandriel and pulled him down onto the floor, kissing him hotly, mouths open and heads angled so Dean, Cas, and Gabe could all see the way his tongue twisted around Samandriel's. Samandriel made small, pleased noises in the back of his throat, his hands curled around Balthazar’s shoulders. Aaron crawled over behind Samandriel, pressing himself against his back and started sucking open-mouthed kisses to Samandriel’s shoulders and up his neck while he reached around to thumb Samandriel’s nipples. Samandriel moaned, his hips rocking forward to rub against Balthazar’s before he ground back into Aaron.

Gabriel groaned and fisted his cock, stroking fast and hard. He flicked the controller and moaned with the increased vibrations. A few more strokes and Gabriel came on his shirt, the black fabric making the white of his come stand out in stark contrast. Dean groaned at the sight and sped up his strokes, reaching down finally to play with his balls. Cas still hadn't touched his cock, though his mouth was dropped open and he panted heavily, each exhale a small whine of pleasure. His cock twitched compulsively against his stomach. 

Gabriel shifted, tipping his head to the side to rest on Cas's shoulder. He flicked the controller again, and Cas arched his back, head pressing into the couch as he moaned loudly. Gabriel started whispering to him, too low for Dean to hear, but whatever it was had Cas scrabbling at the couch, fingers digging in for purchase. His moans picked up in pitch and then Cas came untouched, spurting over his chest and the open fabric of his pants. Dean moaned as he watched and followed Cas over the edge.

He lay there and panted, his eyes cracked open just enough to see the room through the blur of his lashes. He sucked in a deep breath and then another, finally heaving himself upright on the couch and taking in the mess he'd made of his pants and shirt. Benny elbowed him and handed over a few tissues, which Dean took gratefully.

"Well, that was hot," Balthazar said, breaking the silence of their clean up, "but I've got to get going or I'm going to be late." He dropped his balled up tissues into the trash and tugged his clothes back into place. With slaps to shoulders and a few head nods (plus one teasing kiss for Samandriel), Balthazar took off. Benny also stood, already put together.

"I've got to go, too," he said. "Andrea's waitin' for me." Benny checked Dean out, saw that he'd cleaned up and buttoned his pants, and reached out to pull him into a hug. "You gonna come by this weekend?"

Dean dipped his head. "Maybe? Sam's in."

"You know he's always welcome," Benny said even though it wasn't true. Dean nodded agreement.

"I'll text."

Benny slapped his shoulder and said goodbye to others.

Aaron sat on the coffee table, shuffling through menus on the Playstation. "Anyone up for a game?" he asked, pausing on the new Fallout.

Samandriel groaned as he came back from the bathroom, jeans on, his sweats balled up under his arm. "I shouldn't. I've got a ridiculously long paper to write."

"Well, I'm staying," Gabriel said, standing and buttoning his pants. He'd pulled off his shirt and dropped it to the floor, but hadn't pulled on a fresh one. He turned to Cas, who was tucking his shirt into his slacks. "You okay to find your way out, kid?"

"Of course, Gabriel." Cas slung his jacket over his arm.

"I'll walk you out," Dean offered. "Samandriel?"

Samandriel shook his head. "I think I'll go ahead and stay."

"That'a boy!" Gabriel crowed as he wrapped an arm around Samandriel's shoulders and pulled him down between him and Aaron.

"See you guys later then. MOGAI meeting on Thursday?"

"Yeah." Aaron twisted around to meet Dean's gaze. "Your turn for snacks."

"Shit. Okay." He gave Aaron a thumbs up and turned away to find Cas standing by the loveseat, waiting for him. Dean grinned at him and gestured toward the front door.

Outside, Dean paused by the Impala, waiting to see which car Cas climbed into, but Cas didn't walk past. Instead he pushed Dean up against the Impala and kissed him, opening his mouth against Dean's and pressing his tongue in to tease. Dean groaned and clutched at him, kissing back. Cas's body was hot and insistent against his, his weight heavy against Dean. Dean groaned into the kiss and Cas pulled away at the sound. He clutched the lapels of Dean's jacket.

"You are beautiful when you come," he breathed against Dean's mouth, looking into Dean's eyes with a gaze far too earnest for the heat of his kiss and his touch and his body. Dean gaped at him, mouth working as he tried to think of a response. Cas let go and walked away without waiting. He didn't look back at Dean as he headed down the driveway to his car. Dean watched him climb in and drive away, unable to find the strength to do the same.

**Notes for the Chapter:**

> The second chapter is a timestamp of what Gabriel was whispering to Cas to help him come. There’s some threesome fantasizing/dirty talk. ;)


	2. Timestamp: Lend Me Your Ears

**Summary for the Chapter:**

> _Gabriel shifted, tipping his head to the side to rest on Cas's shoulder. [...] Gabriel started whispering to him, too low for Dean to hear, but whatever it was had Cas scrabbling at the couch, fingers digging in for purchase._
> 
> Where Gabriel whispers teasing words into Castiel’s ears.

As the vibrator buzzed against his prostate, Castiel couldn't help but to hate Gabriel, just a little bit, the kind of hate that felt so much like love it made his hips twitch. Gabriel flicked the controls and Castiel gasped, back arching, head pushing against the couch. He rolled his hips down, pushing his ass into the cushion under him in a vain attempt to ride the vibrator like the cock it wasn't.

Gabriel chuckled low under his breath and Castiel turned his head to glare, but his eyes caught on Dean. Dean was watching as Samandriel groaned into his fist where he’d pressed it against his mouth. Dean's hand moved fast and rough over his cock, even as he swallowed heavily, clearly taken with the sight of the young man coming in his pants. Aaron came next and Castiel's attention was drawn away by Balthazar's triumphant laughter. Gabriel flicked the vibrator again and Castiel closed his eyes, panting as pleasure sparked up his spine.

He heard a groan he couldn't identify- _not Gabriel then_ , he thought- and Balthazar said, "Shall we up the ante?"

Castiel cracked his eyes open in time to see Balthazar haul Samandriel from the beanbag chair and drag him into a kiss that Samandriel eagerly returned. As Aaron curled around Samandriel, his hands wandering over his body, Castiel knew Gabriel would not last long- he'd always enjoyed a show, always liked watching someone else's pleasure- and he didn't, flicking up the vibrations so that Castiel was gasping and twitching with it. He heard Gabriel come, the sounds as familiar to him as his own, and wanted to open his eyes to look, but the weight of Gabriel's head against his shoulder, the surge of the vibrator within him again, distracted him.

"He's watching you," Gabriel whispered to him.

Castiel whimpered. He'd known Gabriel had seen his attraction. Worry followed by delight surged through him.

"He's been watching you," Gabriel said, shifting to talk low in Castiel's ear. His breath was heavy and damp against Castiel's neck. He smelled like sweat and come, a scent that drew Castiel back into his memories. Gabriel's voice was wrecked and drowsy. It made him think of the days and afternoons and nights they'd spent together once upon a time. Gabriel continued to whisper in his ear, and his words mixed with Castiel's memories until he was imagining being caught between the two men, Gabriel's firm hands clutching his hips, Dean's unknown mouth pressed against his.

"He wants to touch you, Castiel."

Castiel arched at the thought, grinding down with his hips. He could image what it would be like with the three of them, all hands and mouths and touching.

"I bet he would if he could. Wrap his hands around you, take you into his mouth, into his ass. Or he could fuck you," Gabriel mused. He sighed. "You saw his cock, how big it is, how fat. Image how it'd feel in your mouth or in your ass. He could fuck you so hard, Cassie. I know; he's fucked me so hard I couldn't walk."

Gabriel moaned like Dean was fucking him now. Castiel moaned back, imagining it, imagining Dean behind Gabriel, fucking into him while Gabriel fucked Castiel. Gabriel flicked the vibrations up again and Castiel whined and arched off the couch; he was so close, so close-

"I know, sweetheart," Gabriel breathed. "You should open your eyes and look at him, look at that cock of his."

Castiel obeyed, cracking his eyes open and turning to look. Dean was watching him, eyes on Castiel's cock where it bobbed against his stomach. The sight tipped Castiel over the edge and he twisted the couch cushion in hands, body rolling into it. Dean moaned and came too, clearly caught by the way Castiel had come untouched. Castiel watched him as he trembled through the aftershocks. He was so beautiful, body curving into his orgasm, eyelashes fluttering against his cheeks, mouth open, neck arched. Castiel wanted to climb into his lap, wanted to press his mouth to the muscles there, to the corner of Dean's mouth, to his eyes. He wanted to feel that body pressed up against his own and to feel Dean come on him, _in_ him. Castiel shivered with it and kept watching.

On his shoulder, Gabriel watched Castiel watch Dean.

**Author's Note:**

> While this fic can be read as a stand-alone piece, I ended up writing a significant amount of backstory/extra stuff for this fic. I’m going to post it all as timestamps/a series since I’m not interested in writing it all up as a second full-fledged story. Fair warning: the end-game romantic relationship for this universe is Dean/Cas/Gabe, so the timestamps reflect that. :)


End file.
